(2,4-Dimethoxypyrimidin-5-yl)boronic acid → 5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

HRID 2204407Notes

Reaction equation

HRID 2204407 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](Br)[N:7]([CH:11]([CH3:13])[CH3:12])[CH:6]=1)=[O:4].[CH3:14][O:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[C:19](B(O)O)=[CH:18][N:17]=1.BrC1N(C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=C(Cl)C=CC=3C)C(=O)C=2C=1.C(C1C=CC(OC)=C(B(O)O)C=1)#N>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:19]2[C:20]([O:22][CH3:23])=[N:21][C:16]([O:15][CH3:14])=[N:17][CH:18]=2)[N:7]([CH:11]([CH3:13])[CH3:12])[CH:6]=1)=[O:4]

Participants

5

Reactant 4

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 86703102Methyl 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylateHCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Product 1

HCID 867032195-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step D4) and 2,4-dimethoxypyrimidine-5-boronic acid were used instead of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one and 5-cyano-2-methoxyphenylboronic acid respectively. The title compound was obtained as a yellow solid. tR: 0.97 min (HPLC 3); ESI-MS: tR=0.97 min, [M+H]+ 306 (LC-MS 1); TLC: Rf=0.43 (1:1 EtOAc/heptanes).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-6bffd7ad9dff4276bc7a41bccb9b80d7
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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